First Valentine's Weekend Date Ever...

Yes, I'll be having my first real valentine (weekend) date ever and I don't want to fuck it up. Basically I met this guy here in Chicago New Years Eve at a party, couldn't keep my eyes off him, finally went up to him and we started chatting one thing led to another, i.e. he grabbed my hand, and then we went back to my place, though we did not have sex, just fooled around. He goes to school at Notre Dame and I haven't seen him since, but we've chatted a bit on and off since, now he's coming to visit me next weekend. I really really really do not want to fuck this up! I want to plan things to do, a nice dinner, etc...can you please help someone who is clueless\hopeless romantic out with do's and don'ts?

Here are some ideas I was thinking of doing with him...

Friday Night

Tapas at one of my favorite spots for dinner...ThenGoing to a SpyBar http://www.spybarchicago.com, it's a straight club, but good music and there's definitely gays there...

Saturday Morning:He plays rugby for ND and there are a few matches in six nation tournament this particular weekend, so I was thinking of going to one of those at a pub, the one match is at 10am so maybe we could make it a brunch thing?

Sounds like a nice mix of elegance & fun, along with some romantic elements. Some thoughts:

- Build flexibility and options into your schedule. Nice as it is, avoid giving him the impression that he's on a timed guided tour. Things you've planned can go wrong, and he may not care for some items. Be prepared to offer alternatives at every step, and treat them like they please you should he be the one suggesting them. The last thing you wanna do is appear like you're pouting or irritated because things didn't go exactly the way you had planned.- Your profile, not to mention your screen name, stresses your discreet approach to being gay. Some guys who are completely out really hate that. Being from South Bend one of the attractions of Chicago to which he's looking forward might be its more overt gay scene. Your proposed itinerary, though lovely and very thoughtful regarding his personal interests, is gay-lite. You might wanna get a better feel from him how gay he wants to go, and start educating yourself on the scene, especially if he doesn't know it well himself and might be relying upon you.- Decide in your mind now how you want to handle any sex overtures from him, not wait until they actually happen and get caught unprepared. Whether you have sex or not is immaterial to me, I'm focused rather on your having a smooth response, not freezing with a deer-in-the-headlights reaction. And if you consider that sex might happen, make sure you are presupplied with all the appropriate accoutrements for safe sex.

Frankly a man's decision to remain closeted is his own, and he may have valid reasons for doing it: family, job, community, simple fear, etc. I think being out is the better course in places where homosexuality isn't illegal, but it really is none of my business to push someone through that door.

Rather, my concern is the difficulties in gay dating this can create. And having a gay date was the OP's question here. We haven't been told if the other guy is aware his host is closeted. Maybe he already is and has no problems with it - great!

If the date doesn't know this then the OP may need to take this into consideration in his plans. Maybe it'll be a good opportunity to begin to drop his public veil a little. However it turns out I wish him the best.

Art_Deco saidSounds like a nice mix of elegance & fun, along with some romantic elements. Some thoughts:

- Build flexibility and options into your schedule. Nice as it is, avoid giving him the impression that he's on a timed guided tour. Things you've planned can go wrong, and he may not care for some items. Be prepared to offer alternatives at every step, and treat them like they please you should he be the one suggesting them. The last thing you wanna do is appear like you're pouting or irritated because things didn't go exactly the way you had planned.- Your profile, not to mention your screen name, stresses your discreet approach to being gay. Some guys who are completely out really hate that. Being from South Bend one of the attractions of Chicago to which he's looking forward might be its more overt gay scene. Your proposed itinerary, though lovely and very thoughtful regarding his personal interests, is gay-lite. You might wanna get a better feel from him how gay he wants to go, and start educating yourself on the scene, especially if he doesn't know it well himself and might be relying upon you.- Decide in your mind now how you want to handle any sex overtures from him, not wait until they actually happen and get caught unprepared. Whether you have sex or not is immaterial to me, I'm focused rather on your having a smooth response, not freezing with a deer-in-the-headlights reaction. And if you consider that sex might happen, make sure you are presupplied with all the appropriate accoutrements for safe sex.

Good luck, and do provide details afterwards!

First and foremost, thanks for your input. I definitely agree on planning flexibility into my schedule, I guess this brings up another question, would it be better to surprise him or ask him along the way which he would like to or prefer to do? I did tell him to please tell me if there is something that he would like to do or see, he said he would. I guess I want to do some element of surprise, but I do realize that every event being a surprise might be too much. But I would like to at least surprise him with something, maybe dinner? I just need to book the reservations now, I'm anticipating there being a lot of places being booked during valentine's weekend. But creating flexibility\bbackup-plans should not be a problem.

Yes, I would say I am pretty "gay-lite," in general, he already knows this. If he want to explore more of Boystown, I would be up to this. I spent some time there when I was chasing after a guy 5 years ago, but left it all behind really since then. In any case I do not see myself changing so much with regard to not being into the scene, but who knows, love makes you do strange things right? I will say this, if he and I were in a relationship, I would come out, I think it might not be right away, but after a month or two, if we are still madly in love, I would come clean.

As for sex, it wouldn't be my first time, I am prepared in terms of having all the necessary "equipment" for safe sex. I would be open to this for sure, so I don't think there will be any deer in the headlight moments, however I do have another thread at the moment regarding this...in terms of improving the experience.

Frankly a man's decision to remain closeted is his own, and he may have valid reasons for doing it: family, job, community, simple fear, etc. I think being out is the better course in places where homosexuality isn't illegal, but it really is none of my business to push someone through that door.

Rather, my concern is the difficulties in gay dating this can create. And having a gay date was the OP's question here. We haven't been told if the other guy is aware his host is closeted. Maybe he already is and has no problems with it - great!

If the date doesn't know this then the OP may need to take this into consideration in his plans. Maybe it'll be a good opportunity to begin to drop his public veil a little. However it turns out I wish him the best.

He already knows I'm closeted. I also told him I'm waiting to have a relationship with a man before I come out, and he is fine with this.

I like the ideas you have it sounds like you put a lot of time into it! If I was on a date with a guy I really liked though, I'm not sure if I'd like to go to a bar or not. Maybe if we had been dating for awhile and wanted to get out of the house. But for a romantic date, I would like to do some more creative stuff just by ourselves. Good luck man!

wyojock saidI like the ideas you have it sounds like you put a lot of time into it! If I was on a date with a guy I really liked though, I'm not sure if I'd like to go to a bar or not. Maybe if we had been dating for awhile and wanted to get out of the house. But for a romantic date, I would like to do some more creative stuff just by ourselves. Good luck man!

Thanks, well last time we spoke he mentioned he's never been to boys town, so maybe it's something we should do? Maybe I should ask him?

wyojock saidI like the ideas you have it sounds like you put a lot of time into it! If I was on a date with a guy I really liked though, I'm not sure if I'd like to go to a bar or not. Maybe if we had been dating for awhile and wanted to get out of the house. But for a romantic date, I would like to do some more creative stuff just by ourselves. Good luck man!

Thanks, well last time we spoke he mentioned he's never been to boys town, so maybe it's something we should do? Maybe I should ask him?

Yep I would ask him! It might just be his personal preference compared to mine, and maybe he would enjoy going out.

NewNDiscreet saidIf these ideas sound fun to you guys...if there's any suggestion additional points to add, I don't want him to be bored here!

Sounds like you have a very good handle on this. And I'm glad to hear he knows you're closeted. Nothing more is necessary on that topic.

You mention earlier about surprises, and I agree the entire weekend shouldn't all be that way. But at least one surprise is nice.

A little souvenir object of Chicago could be thoughtful, possibly engraved with his name and date, wrapped as a gift. I love to give photographs, though that would likely have to wait until after the trip. A picture of you 2 together, framed.

I have a true digital photo printer, so I can make quality prints on photo stock in seconds. And spare picture frames are on hand. Really, I do! I make a quick edit & print, put it in the frame, and present it. Even in this day of digital photography that still impresses people. It's the ultimate personal gift, and he'll think of you every time he sees it.

Other surprises I've arranged have required tight timing, and I don't know what your transportation is, and how it might fit into your overall schedule. My favorite is the nonchalant approach, we're just walking or driving along, and I casually drop into some restaurant.

Once inside he realizes the whole thing has been prearranged, as we're welcomed by name, a table set aside and things like wine or champagne waiting for us. My own husband will get this treatment on Valentine's Day, though with a few hours notice beforehand when he gets his card around 5 PM and finds a certificate to his favorite restaurant attached, for 7 PM that night. I'm making the arrangements with the owner now, everything in place when we arrive, him treated like royalty, a gift already there awaiting him, the meal prepaid.

I just love doing this shit, and it sounds like you have a flair for it, too. As I often say to our friends: "Are we not gay?"

Frankly a man's decision to remain closeted is his own, and he may have valid reasons for doing it: family, job, community, simple fear, etc. I think being out is the better course in places where homosexuality isn't illegal, but it really is none of my business to push someone through that door.

Rather, my concern is the difficulties in gay dating this can create. And having a gay date was the OP's question here. We haven't been told if the other guy is aware his host is closeted. Maybe he already is and has no problems with it - great!

If the date doesn't know this then the OP may need to take this into consideration in his plans. Maybe it'll be a good opportunity to begin to drop his public veil a little. However it turns out I wish him the best.

Now Artie why does that not apply when it's concerning a Republican, or a Republican politician with a family, and because of his job and position he can not come out either; if your statement does not apply to all, we must dismiss it as nothing more than something self serving; after all you have lived most of you very long life as a straight man.

But all the best to the OP.

Maybe Artie can arrange a candle light supper for you both, with all the right kind of people.

Dude, you've planned out a lot of great things. It's the thought that counts, and you definitely seem like a thoughtful guy. If he's a good guy, he will appreciate all the effort you put into the weekend no matter what you do.

Alright got into the signature room...it's in the same building as the indoor ice rink, however dinner requires business casual attire, and it would be awkward to go back and forth or go skating in business casual no? What do you guys think?

NewNDiscreet saidIf these ideas sound fun to you guys...if there's any suggestion additional points to add, I don't want him to be bored here!

Sounds like you have a very good handle on this. And I'm glad to hear he knows you're closeted. Nothing more is necessary on that topic.

You mention earlier about surprises, and I agree the entire weekend shouldn't all be that way. But at least one surprise is nice.

A little souvenir object of Chicago could be thoughtful, possibly engraved with his name and date, wrapped as a gift. I love to give photographs, though that would likely have to wait until after the trip. A picture of you 2 together, framed.

I have a true digital photo printer, so I can make quality prints on photo stock in seconds. And spare picture frames are on hand. Really, I do! I make a quick edit & print, put it in the frame, and present it. Even in this day of digital photography that still impresses people. It's the ultimate personal gift, and he'll think of you every time he sees it.

Other surprises I've arranged have required tight timing, and I don't know what your transportation is, and how it might fit into your overall schedule. My favorite is the nonchalant approach, we're just walking or driving along, and I casually drop into some restaurant.

Once inside he realizes the whole thing has been prearranged, as we're welcomed by name, a table set aside and things like wine or champagne waiting for us. My own husband will get this treatment on Valentine's Day, though with a few hours notice beforehand when he gets his card around 5 PM and finds a certificate to his favorite restaurant attached, for 7 PM that night. I'm making the arrangements with the owner now, everything in place when we arrive, him treated like royalty, a gift already there awaiting him, the meal prepaid.

I just love doing this shit, and it sounds like you have a flair for it, too. As I often say to our friends: "Are we not gay?"

A question concerning the souvenir, and everyone feel free to chime in. Given the experiences I have had, I tend to believe guys don't like me unless proven otherwise and I don't know what that otherwise would be in this particular situation. Although this guy is coming to see me, I still am apprehensive of getting him a souvenir to remember me by, I feel like it comes off too strong? Would it be appropriate in this situation? Or should I wait...ehh I never know with these things, I'd almost rather he forget me if it doesn't work out...and I forget him.

Get him a T shirt and a small key chain of where you take him. Then he will think of you when he uses his keys.Have fun, make it fun for him and I agree leave plans open ended in case he has some of his own.

MikemikeMike saidGet him a T shirt and a small key chain of where you take him. Then he will think of you when he uses his keys.Have fun, make it fun for him and I agree leave plans open ended in case he has some of his own.

Both or either of those gifts should be OK. Get one for each of you. A generic Chicago-themed T-shirt shouldn't necessarily later cause sweaty flashbacks should this date be a fiasco.

(No, Bob, don't even suggest that possibility, it's gonna go fine)

Souvenir keychain is good, too. Doesn't have to be something he'll use everyday. I've literally got dozens, and the souvenir ones end up being tags for the less-used keys we keep on hooks or in drawers, not our daily keys in our pockets.

NewNDiscreet saidAlright got into the signature room...it's in the same building as the indoor ice rink, however dinner requires business casual attire, and it would be awkward to go back and forth or go skating in business casual no? What do you guys think?

Are you arriving by car, in which you could have extra clothes? Does current business casual attire in Chicago include polos, or a simple long-sleeved button front shirt? (I forget it's winter up there)

Trousers or slacks could be a challenge, would need a place to change for those, maybe the rink has a locker room, and of course spoils some of the surprise element of nonchalantly popping into the Signature Room. But I like the idea that skating gets him near the restaurant, so you can time your arrival for the reservation much better. Been years since I was in Chicago, but the SR is a brilliant idea, no better way to "see" the city, and can be very romantic. Dinner at dusk can be incredible, as the sun sets and the city's lights turn on.

Explaining why you're bringing an extra set of clothes shouldn't be too difficult - you need jeans for skating, which I presume he already knows he's doing (or if not, just say it's more comfortable to knock around the city), but you guys might drop into a restaurant or bar that caters to the business set, and you wanna be prepared, Chicago being Chicago. Plus your skating clothes might have gotten wet from tumbles on the ice.